‘Tis the season for holiday pop-up bars. Some of Chicago’s favorite bars and restaurants have temporarily transformed their space into full-blown winter wonderland, with over-the-top decorations, seasonal cocktails, festive food specials, and plenty of photo opps. And don’t wait — many of these seasonal extravaganzas disappear after the new year.

Celebrate the season at these festive Christmas and holiday bars and pop-ups in Chicago.

Santa Baby Christmas Bar

Photo by Kailley Lindman Photography

Nov. 21, 2024 – Jan. 5, 2025
If you want to go all in on the holidays, why not celebrate at this over-the-top Christmas experience? Santa Baby at Bamboo Club in Wrigleyville features extensive decor in every inch of their space, from twinkling lights outside to ceilings crowded with glittering ornaments inside. And the boozy holiday drinks are just as extravagant — get cocktails like the Merry Mojito, Jingle Juice, Yule Mule, and spiked hot chocolate and egg nog in individual and jumbo shareable sizes. Plus, check out weekly events like holiday trivia, bingo, and themed paint and sips.

Book your table inside the multi-level bar area or check out the tented patio outfitted with heaters. Make your reservations here.

8 Crazy Nights at The Graystone Tavern

Nov. 27, 2024 – Jan. 5, 2025
8 Crazy Nights, Chicago’s first Hanukkah-themed pop-up, is returning to The Graystone Tavern in Lakeview. The event will take over the bar and the enclosed, weatherproof patio, which will both be decorated with dreidel ornaments, lighted menorah decor, a photo booth, and more than 30,000 blue and white lights.

A special food menu includes traditional favorites like challah grilled cheese, matzo ball soup, brisket sandwiches, and boozy jelly donuts. There’s also a playful drink menu with cocktails (like the Gelt Martini), beers, and shots.

River North Pole at Three Dots and a Dash

Nov. 15, 2024 – Jan. 5, 2025
One of the city’s most famous tiki bars is going polar this winter. Three Dots and a Dash is hosting a River North Pole bar takeover, turning their tropical paradise into a snowy winter wonderland with winter and holiday decorations throughout the downtown space. Enjoy expertly mixed cocktails like the Mistletow Mai Tai, Hot Buttered Rum, Candy Cane Swizzle, and more. Make your reservations today.

Winter Wonderland at JoJo’s Shake Bar

Jojo's Shake Bar
Jojo’s Shake Bar

Now open
In River North, JoJo’s Shake Bar has launched their expansive Winter Wonderland pop-up, decking out every inch of their space in festive decor. Try their over-the-top holiday shakes and Santa-approved cocktails, like the giant Polar Espresso Martini and Santa Sangria. Plus, check out special themed events like Holly Jolly Mixology Classes and Gingerbread House Decorating. Reservations are now available.

Tinseltown at Pink Squirrel

Tinseltown at Pink Squirrel
Tinseltown at Pink Squirrel

Now open through Dec. 31, 2024
This cocktail spot in Logan Square, an homage to Midwestern bar culture, totally transforms itself for the holidays. Tinseltown at Pink Squirrel includes wall-to-wall decorations for a truly immersive experience, along with a full menu of festive treats that includes shots, cocktails, punches, and milkshakes.

Guests are also invited to decorate their own holiday cookies or play a few rounds of duckpin bowling. Make reservations for bowling lanes and holiday events in advance.

A Very Dandy Holiday at The Dandy Crown

Nov. 22, 2024 – Jan. 4, 2025
A Very Dandy Holiday bar is back by popular demand at The Dandy Crown. Cocktails are the main draw at this West Town spot, where the award-winning bartenders will be serving up a series of themed drinks all season long. Expect festive glassware, immersive decor, and plenty of yuletide cheer. Check the calendar for fun holiday happenings like visits from Santa, holiday trivia, ugly sweater nights, a New Year’s Eve party, and more.

Rudolph’s Holiday Winter Igloos

LH Rooftop Chicago decorated for the holidays
LH Rooftop

Nov. 16, 2024 – Jan. 31, 2025
Enjoy sweeping city views and tons of holiday cheer at Rudolph’s Rooftop. Located on the 22nd floor of the LondonHouse Chicago, this seasonal pop-up includes festival menu items, hot and cold cocktails, cozy heated igloos, holiday décor, and backdrops for capturing photos. Not to mention the stunning views of the Chicago River and the surrounding city lit up for the holidays. Contact rsvp@londonhouse.com to book your tables and private igloos.

Explore more: Keep the festive fun going at these winter rooftops and igloos in Chicago.

Happy’s at the Chicago Athletic Association

Photo by Lyndon French

Dec. 4 – Dec. 21, 2024
Head to the historic Chicago Athletic Association in the Loop for Happy’s Bar, their annual Christmas pop-up bar. Billed as “an over-the-top explosion of holiday cheer”, Happy’s is taking over the ground floor of the historic hotel for the seventh year. Patrons will be greeted with cozy winter cocktails and bar bites, favorite festive tunes, and lots and lots of glittering lights.

Jack Frost Christmas Pop-up

Nov. 29, 2024 – Jan. 5, 2025
This outdoor winter extravaganza has something for all ages, from picking out the family Christmas tree to sipping boozy holiday drinks. Jack Frost Christmas Pop-up in Fulton Market invites guests to enjoy ice skating, axe throwing, bumper cars, music and lights, seasonal drinks, and more. Plus, there are plenty of fun photo opps scattered throughout the decked-out space.

Get your tickets for admission and activities in advance.

More Christmas bars and holiday pop-ups in Chicago